Rapid multistep synthesis of a bioactive peptidomimetic oligomer for the undergraduate laboratory

Yeliz Utku; Abhinav Rohatgi; Barney Yoo; Kent Kirshenbaum; Ronald N. Zuckermann; Nicola L. Pohl

doi:10.1021/ed100202f

Rapid multistep synthesis of a bioactive peptidomimetic oligomer for the undergraduate laboratory

Yeliz Utku, Abhinav Rohatgi, Barney Yoo, Kent Kirshenbaum, Ronald N. Zuckermann, Nicola L. Pohl

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Peptidomimetic compounds are increasingly important in drug-discovery applications. We introduce the synthesis of an N-substituted glycine oligomer, a bioactive "peptoid" trimer. The six-step protocol is conducted on solid-phase resin, enabling the synthesis to be performed by undergraduate organic chemistry students. This synthesis lab was successfully completed within one 4-h session by second-year students. The procedures are relatively inexpensive and versatile, enabling modifications to generate a variety of oligomer sequences from commercially available reagents including bromoacetic acid and a diverse set of primary amines.

Original language	English (US)
Pages (from-to)	637-639
Number of pages	3
Journal	Journal of Chemical Education
Volume	87
Issue number	6
DOIs	https://doi.org/10.1021/ed100202f
State	Published - 2010

Keywords

Combinatorial chemistry
Drugs/pharmaceuticals
HPLC
Hands-on learning/manipulatives
Laboratory instruction
Mass spectrometry
Medicinal chemistry
Nucleophilic substitution
Organic chemistry
Proteins/peptides
Second-year undergraduate
Synthesis
Thin layer chromatography

ASJC Scopus subject areas

General Chemistry
Education

Access to Document

10.1021/ed100202f

Cite this

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AU - Utku, Yeliz

AU - Rohatgi, Abhinav

AU - Yoo, Barney

AU - Kirshenbaum, Kent

AU - Zuckermann, Ronald N.

AU - Pohl, Nicola L.

PY - 2010

Y1 - 2010

N2 - Peptidomimetic compounds are increasingly important in drug-discovery applications. We introduce the synthesis of an N-substituted glycine oligomer, a bioactive "peptoid" trimer. The six-step protocol is conducted on solid-phase resin, enabling the synthesis to be performed by undergraduate organic chemistry students. This synthesis lab was successfully completed within one 4-h session by second-year students. The procedures are relatively inexpensive and versatile, enabling modifications to generate a variety of oligomer sequences from commercially available reagents including bromoacetic acid and a diverse set of primary amines.

AB - Peptidomimetic compounds are increasingly important in drug-discovery applications. We introduce the synthesis of an N-substituted glycine oligomer, a bioactive "peptoid" trimer. The six-step protocol is conducted on solid-phase resin, enabling the synthesis to be performed by undergraduate organic chemistry students. This synthesis lab was successfully completed within one 4-h session by second-year students. The procedures are relatively inexpensive and versatile, enabling modifications to generate a variety of oligomer sequences from commercially available reagents including bromoacetic acid and a diverse set of primary amines.

KW - Combinatorial chemistry

KW - Drugs/pharmaceuticals

KW - HPLC

KW - Hands-on learning/manipulatives

KW - Laboratory instruction

KW - Mass spectrometry

KW - Medicinal chemistry

KW - Nucleophilic substitution

KW - Organic chemistry

KW - Proteins/peptides

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Rapid multistep synthesis of a bioactive peptidomimetic oligomer for the undergraduate laboratory

Abstract

Keywords

ASJC Scopus subject areas

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